Ammonium Chloride → HCID 11222684、化合物

HRID 2102311

反応式

HRID 2102311 の反応式
[Li]CCCC.[N:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]3[CH2:19][CH2:18][CH2:17][C:14]3=[N:15][N:16]=2)=[CH:8][CH:7]=1.Br[CH2:21][C:22]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[O:24][N:23]=1.[NH4+].[Cl-]>C1COCC1>[Cl:33][C:29]1[CH:28]=[C:27]([C:25]2[O:24][N:23]=[C:22]([CH2:21][CH:17]3[C:14]4=[N:15][N:16]=[C:12]([C:9]5[CH:8]=[CH:7][N:6]=[CH:11][CH:10]=5)[N:13]4[CH2:19][CH2:18]3)[N:26]=2)[CH:32]=[CH:31][CH:30]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 8531463-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazoleHCID 57837945HCID 57837945、化合物HCID 178418339Butyllithium

生成物 1

HCID 11222684HCID 11222684、化合物収率 1.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

nBuLi (2.5 M, hex., 600 μl) was added to a solution of 3-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole (250 mg, 1.33 mmol) in THF (13 ml) at 0° C. After 10 min the reaction mixture was cooled to −78° C. and 3-(bromomethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole (400 mg, 1.46 mmol) in THF (10 ml) was added. After stirring at −78° C. for 30 min stirring was continued at 0° C. reaching r.t. o.n. Aq. sat. NH4Cl was added and the mixture was extracted with EA. The organic phase was washed with water and brine, dried and concentrated. Flash chromatography (DCM/MeOH 40:1) followed by preparative HPLC afforded 6.5 mg (1%) of the title compound. 1H NMR: 2.72 (m, 1H), 3.13 (m, 2H), 3.62 (m, 1H), 3.93 (m, 1H), 4.31 (m, 2H), 7.47 (t, 1H), 7.56 (m, 1H), 7.74 (d, 2H), 7.98 (m, 1H), 8.08 (m, 1H), 8.74 (m, 2H).

後処理

  1. stirringstirring
  2. customwas continued at 0° C.
  3. customreaching r.t.
  4. extractionthe mixture was extracted with EA
  5. washThe organic phase was washed with water and brine
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-784112aa20f04fc9b3af6e390e476814
出典データセット
uspto-grants-2009_08
特許番号
US07576077B2

関連ノート

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